Quinolin compounds and process of producing the same.



' T all'whom it may concern:

ALnxn-DA-vis, or INDI ANAr-oLIsJNDIANA, Ass'Ie onroiTHE ELI LILLY AND "COMPANY, OF INDIANAroLIs, INDIANA, A CORPORATION or NDIANA.

oUINoLIN oo /irouNDs,AND PRooEss or rnoDuoING TnEsA'mE.

No Drawing.

Beit known that I, ALEX B. DAvIs, a citizen of the United States, residing at Indianapolis, Marion county, and State ofIndiana, have invented and discovered certain new and useful Improvements 'in'Quinolin Compounds and Process of Producing the'Same, of which the following is a specification.

My invention relates to compounds of the quinolin series and process of roducing them. These compounds are use ul as mobilizers for uric acid.

The compounds are all "derivedifrom' (2) para-oXy-meta-methoxy-phenyl quinolin (4)0arboxyli'c acid, and are produced by boiling together in absolute alcoholic solution, equimolecular proportions of an aromatic amin, pyruvic acid and vanil1in(paraoxy meta methoxy benzaldehyde). Thus from the toluidins and anisidins there are' formed the corresponding substituted quinolin compounds on boiling them with equimolecular proportions of pyruvic acid and vanillin in absolute alcoholic solution, ortho, meta, and para anisidin, and ortho, meta, and para toluidin yield respectively: (2) para-oXy-meta-methoxy-phenyKS) methoxy-quinohnbl) carboxylic acid. (2) paraoxy-mcta-methoxy phenyl(7)methoxy quinolin(4)carboxylio acid. (2)para-oxy-meta-. methoxy-phenyl(6)methoXy-quinolin(4) carboxylic acid. (2)para-oxy-meta-methoxyphenyl(8)methyl-'quino1in(4)carboxylic acid. (2) para-oxymeta methoxy phenyl (7) methylquinolin (4) carboxylic acid. (2) paraoxy-meta-methoxy-phenyl (6) methylquinolin (4) carboxylic acid. These com pgunds may be represented by the following formula:

in which X is an organic radicalreplacing-a hydrogen atom in one of the OH groups of the quinolin ring.

The last named compound of the group of Specification of Letters Patent. Patented May 11 1915, Application med February 21, 1913. Serial No. 750,024-

" ii-on o-cm If para amino-ethyl-benzoate be the amin used, then the product is (2)para-oXy-meth oxy-phenyl-quinolin (4B) (6) dicarboxylic acid- 6") ethyl-ester.

In carrying out the process in detail, one may proceed as follows: In a vessel provided with a reflux condenser, there is placed 76 parts b weight of vanillin, 180 parts of absolute alcohol, and 54 parts of para-toluidin. It is thenheated to boilin and allowed to boil 15 minutes. 44 parts 0 pyruvic acid diluted with its own volume of absolute alcohol, are then allowed to slowly flow in over a period of T1,; hour, and the, resulting mass boiled three hours It is then set aside for twenty-four hours, when the quinolin compound crystallizes out.- It is filtered off and recrystallized from alcohol, when it appears as Very fine deep orange colored crystals. 1 The compound produced as above will be (2) para oXy meta methoxyophenyl (6) methyl-quinolin (4) carboxylic aid.

The method of purification may vary somewhat from the above according to the properties of the particular compound produced. 85

1. Compounds of the quinolin l) carboxylie acid group, containing a para-oXy-metamethoxy-phenylgroup in the 2 position in the quinolin ring.

2. Compounds of quinolin having the following formula:

hydrogen atom in one of the CH groups of the quinolin ring.

I which may be called (2) para-oxy-meta-methoxy-phenyl (6) methyl-quinolin (4) carboxylic acid.

as an X 2| u l in which X is an organic radical replacing a ALEX DAVIS. a 5.1

Witnesses C. W. SHOWALTER, FRANK R. ELDRED.

copieaofthis patent may be obtained for five cents each, by addressing the Commissioner of Patents,

Washington, D. 0. 

